Gilmore Girls ‘ship watch: Season 5

I have to say, it feels a little off-topic to discuss Rory’s love life at the end of season 5 when her relationship with her mother is so clearly the one in need of analysis, but alas, this is what I have committed to. It’s not that there isn’t plenty to say when it comes to Rory’s love life. There’s just a lot more to say about Lorelai and the mother/daughter relationship that is coming apart at the seams. The Unraveling Lorelais, if you will. Perhaps there will be another column.

Let’s focus on the matter at hand: Rory and Dean dated again. I’ll admit, I did not see that coming. I was sure the sex was a one time deal. I must confess that I find sexually active Dean extremely appealing, but that’s not particularly relevant to this discussion. Anyway, I’m likely in the minority, but I actually enjoyed this little reunion. So often we wonder “what would have happened if…” Rory and Dean don’t have to wonder. They outgrew each other. They would have outgrown each other no matter what. The end of their relationship this time around is exactly how it would have ended had they stayed together the entire time. Without Jess, without Lindsay–this is where Dean and Rory were always destined to land: at the realization that they are heading in two completely different directions.

I’ve heard fans echo the sentiment that Dean expresses at one point, that he “gave everything up” for Rory. I, however, would argue that Dean gave up nothing. The life he had with Lindsay was a sham. He didn’t love her. He never loved her. Perhaps he could have found a way to be happy with her on some level, but Lindsay deserves more than that. Cheating on Lindsay was wrong, but at the end of the day the fact that Dean and Lindsay split up before having children means they both get a chance to find real, reciprocated love. The tragedy of Dean will be if he is still single and miserable and pining after Rory in the reboot. If he moves on from this mistake, fully able to move past Rory Gilmore and ready to start the rest of his life, then honestly, everybody wins.

I wouldn’t put myself on Team Dean if that means thinking that Dean is Rory’s soulmate. He certainly is not. But I love Dean for who he was to her when he was in her life. I’m still not sure how I feel about the other two, so I can’t fully rank them.

Speaking of which, hello Logan Huntzberger! Logan is the kind of character that I would typically hate. He’s smarmy and smug and rich and gross. Two things, though. One, it’s Matt Czuchry, so it’s nearly impossible to hate him. And two, he does all the right things when it comes to Rory. It’s true, he’s entitled and his friends are the worst. But, considering he told Rory he couldn’t do the whole boyfriend thing, he’s really stepped up at almost every turn. He clearly really cares about her.

If Rory were to continue to just be Rory instead of morphing into this unrecognizable person right before our eyes, Logan might have been the perfect match for her. Her moral center plays a good balance to his recklessness. The problem is that Rory is coming undone. In the face of her epic meltdown, she needs someone who will help point her back to center. Logan, for all the good qualities he has surprised me with, is not that person. If anything, he finds her rashness exhilarating and enjoy that she isn’t fighting him on some of his crazier whims. Had Rory suggested stealing a boat to almost anybody else she’s ever known, the person would have convinced her she was insane and that would have been the end of it. Logan enjoys this sort of thing. The combination just can’t be good. Though I wouldn’t say Rory’s behavior was caused by Logan’s influence, his willingness to support her in her bad choices is likely to be a problem.

And yet, I still like Logan. He cares about Rory and he wants to see her succeed. I’m very interested to see where their relationship is headed and what the season 6 circumstances are for Jess’s return. See you back here real soon! Final thoughts are just a couple of weeks away!